Nitric Acid → 4-Hydroxy-7,8-dimethyl-2H-1-benzopyran-2-one

HRID 1283308Notes

Reaction equation

HRID 1283308 reaction equation
[N+]([O-])(O)=O.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:18])=[C:13](C)[C:14]=2C)[O:9][C:8](=[O:19])[CH:7]=1.[CH:20](Cl)(Cl)Cl>>[CH3:18][C:12]1[C:11]([CH3:20])=[C:10]2[C:15]([C:6]([OH:5])=[CH:7][C:8](=[O:19])[O:9]2)=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6212ChloroformHCID 547321174-Hydroxy-5,6,7-trimethyl-2H-1-benzopyran-2-one

Product 1

HCID 547171114-Hydroxy-7,8-dimethyl-2H-1-benzopyran-2-one

Procedure

Fuming nitric acid (18 ml) was added to a stirred suspension of 4-hydroxy-5,6,7-trimethylcoumarin (m.p. 262°-4°; 3.38g) in chloroform (250 ml) at room temperature over 1.5 hours. After a further 30 minutes, the solvent was removed in vacuo at room temperature and 6N hydrochloric acid (70 ml) added to the residue. Filtration gave the product, m.p. 134°-7°(d), (C12H11NO5 requires C, 57.83; H, 4.45; N, 5.62. Found: C, 57.92; H, 4.57; N, 5.65).

Workup

  1. customthe solvent was removed in vacuo at room temperature
  2. addition6N hydrochloric acid (70 ml) added to the residue
  3. filtrationFiltration

Sources & evidence

ORD record
ord-bf25204593814f90a151a4478f784236
Source dataset
uspto-grants-1976_08
Patent number
US03974289

Reaction notes

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